Diisopropylamine → 1-(2-Diisopropylaminoacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline

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Reaction Steps

A mixture of 1-(2-chloroacetyl)-7-nitro-1,2,3,4-tetrahydroquinoline (D8) (6.7 g, 26 mmol) and diisopropylamine (50 ml) in THF (50 ml) was heated at reflux for 5d then cooled to room temperature. Aqueous work-up yielded a crude oil which was purified by flash column chromatography. Elution with 0-5% methanol/DCM gave the title compound as a dark oil (6.56 g). 1H NMR (250 MHz, CDCl3) δ (ppm): 8.62 (br, 1H), 7.91 (dd, 1H), 7.27 (d, 1H), 3.95 (m, 2H), 3.54 (s, 2H), 3.02 (sp, 2H), 2.87 (t, 2H), 2.02 (m, 2H), 1.02 (d, 12H).

Provenance & Evidence